Why won't ArGIS Online keep me logged in for two weeks? Sometimes it is less than a day.

I check the box that says "Keep Me Signed In" every time I log in. Sometimes it keeps me logged in for a few days. More often, it logs me out as soon as I close ArcMap, the same day. Is anyone else having this issue? Any ideas for how to solve it?

This appears to be normal behaviour even on GeoNet and on other product sites. I usually take the 'keep me signed in' to mean 'keep me signed as long as your server will let me' Sometimes you might see a re-sign in process but other times, you just have to log back in. It remains a challenge for those that have a difficult password or dozens to remember